Vacation rentals in Andersonville

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Top-rated vacation rentals in Andersonville

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Guest favorite

A gated entryway is visible, featuring a wooden fence painted in a neutral tone. The gate is partially open, leading into a green space lined with trees and plants. The house entrance is seen in the background, with a clear sky above.

Apartment in Edgewater

4.93 out of 5 average rating, 453 reviews

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Top guest favorite

A red brick three-flat building is presented with large windows and intricate architectural details. Colorful pumpkins are arranged in the front garden, which features lush greenery and blooming flowers. A rainbow flag is displayed prominently by the entrance, adding a touch of vibrant color.

Apartment in Andersonville

5 out of 5 average rating, 122 reviews

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

Top guest favorite

The living area features a comfortable blue sofa adorned with decorative cushions, complemented by a patterned rug. A soft pink armchair and a small round coffee table are present. A vibrant floral painting hangs on the wall, and natural light enters through the window covered by light curtains.

Guest suite in Andersonville

4.96 out of 5 average rating, 380 reviews

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

Top guest favorite

A spacious living room is featured, with a large blue sofa adorned with pink cushions. Two cozy armchairs with blue upholstery flank a glass coffee table, which is positioned on a decorative area rug. A television stands against the wall, while soft lighting illuminates the space.

Apartment in Andersonville

4.98 out of 5 average rating, 266 reviews

Foster Flat - Retreat to your Home Away from Home

The perfect place to stay for your next trip to Chicago. This fully furnished 2 bedroom/1 bath unit features bright living spaces with modern decor. Located just a few blocks from the heart of Andersonville, you'll find coffee shops, restaurants, shopping and nightlife. Lincoln Square and Ravenswood neighborhoods are also nearby for you to explore. Conveniently located to public transportation (buses, Red and Brown Line trains, as well as Metra), you'll have no trouble getting around town.

Top guest favorite

The bright living area features a grey sofa adorned with colorful cushions. Two teal chairs are positioned nearby, adding a pop of color. Natural light floods the space through oversized windows, highlighting the vibrant artwork on the wall and a modern coffee table at the center.

Apartment in Andersonville

4.95 out of 5 average rating, 577 reviews

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

Guest favorite

A spacious backyard features a wooden deck leading to a gravel area with green grass. Outdoor seating options include a dining table, lounge chairs, and a fire pit area. Trees and buildings frame the background, under a clear blue sky.

Apartment in Edgewater

4.98 out of 5 average rating, 143 reviews

Free street parking - Backyard Oasis

Fun & Funky Andersonville Retreat at Midwest Traveling offers a private chef experience during your stay - reach out for more info! A spacious basement unit that we (the owners) live above. We do have a mini golden doodle on site and if you’d like to meet him just reach out and we can make that happen :) he loves meeting our friendly guests! Andersonville is recognized as one of the coolest neighborhoods worldwide according to Time Outs magazine (Oct 21)

Superhost

A spacious king size bed is dressed in a dark blue patterned quilt, complemented by decorative pillows. A vibrant red throw rests at the foot of the bed. The room features wooden accents, a mirror, and a small bookshelf. Decorative wall hangings add character.

Guest suite in Andersonville

4.86 out of 5 average rating, 380 reviews

Cozy and Private Andersonville Retro Studio

In the heart of Andersonville, this cozy, vintage-inspired studio apartment can be your home away from home. Located on the garden level, it is only 2 steps down to your own private oasis in the city. Separate private building entrance and no shared spaces in the entire basement suite. Sparkling clean and every detail considered for your comfort. Enjoy living like a local steps from Chicago's best 'hood, while experiencing the comforts of home.

Top guest favorite

A spacious living area is adorned with floral wallpaper, featuring a comfortable gray sofa and a wooden coffee table. Two white chairs are positioned around a woven rug. An open kitchen area is visible, equipped with modern appliances and green bar stools at the counter.

Apartment in Andersonville

4.93 out of 5 average rating, 155 reviews

Andersonville's Secret Garden: 2 beds, 1 bath

This serene retreat is tucked away amongst the tree-lined streets of the Lakewood Balmoral historic district. Guests can venture just two blocks to dive into the hustle and bustle of Andersonville, with its incredible food scene and unique local shopping spots. Those looking to explore all that Chicago has to offer will enjoy easy access to the CTA redline, major bus routes, and Divvy stations (our shared bike provider).

Top guest favorite

A cozy living room is presented with a soft area rug and a contemporary ceiling fan. Two armchairs in vibrant colors face a stylish sofa adorned with decorative pillows. A coffee table sits in the center, while a large mirror and art piece add visual interest to the space.

Apartment in Edgewater

4.97 out of 5 average rating, 109 reviews

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.

Top guest favorite

The living room features warm pine walls, offering a cozy atmosphere. A dark, spacious sofa is positioned alongside a wooden coffee table. Two lamps illuminate the space, framed artwork adorns the walls, and potted plants are placed on the windowsill, adding a touch of greenery.

Guest suite in Andersonville

4.98 out of 5 average rating, 142 reviews

Cozy Andersonville Cabin

Our cabin-in-the-city is a relaxing garden apartment, located in the popular LGBTQ+ friendly Andersonville area of Chicago. The cabin unit is decorated in bear and nature themes, with warm and cozy pine walls - like you were renting a cabin in the woods! Our place is a half a block from the main strip. Plenty of great shopping, award winning dining, and fun night life is just steps from our house!

Top guest favorite

A bright living room features hardwood flooring and a large, comfortable gray sectional sofa. Two unique yellow chairs are positioned nearby. A stylish TV unit and shelves display decor items, while light streams in through multiple windows, enhancing the open and inviting layout.

Apartment in Lincoln Square

4.98 out of 5 average rating, 180 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

Welcome to this thoughtfully remodeled 1925’s two-flat building located in the Second Coolest Neighborhood in the US. While this stylish space is the perfect relaxing stay, its location makes it easy for you to get around. *Free street parking You are only: 5 min walk to Clark St & Exceptional restaurants & bars 6 min drive to Lakefront & Lakeshore Drive... 17 min drive to Downtown Chicago...

Top guest favorite

A cozy living area is presented with a dark sofa and a wooden coffee table atop a patterned rug. Exposed brick walls and timber beams enhance the aesthetic. A decorative bicycle hangs on the wall, complemented by shelves displaying art and greenery.

Apartment in Andersonville

4.96 out of 5 average rating, 110 reviews

Andersonville Bicycle Studio

Enjoy a stylish experience at this centrally-located Andersonville studio. The Bicycle Studio leaves no detail untouched - modern amenities with the charm of exposed brick and timber beams. You are two blocks away from Chicago's popular Andersonville neighborhood - endless dining, shopping and entertainment. Quick access to public transportation and Chicago's lakefront.